This one is kinda broken.
(Can be unlocked in the same playthrough as well as getting the “Abdul-Jabar Who? achievement)
There’s a weird glitch where depending on if you don’t make the ball into the hoop it still counts as you winning for some reason.
However that hasn’t been the case with me, just aim your shot away from the hoop and you should unlock the achievement when the basketball challenge is over.
However if you don’t lose the challenge, immediately quit the game and load back up the auto save depending on which saved game you have the basketball challenge on.
Repeat this process until the achievements pops, I had to try this at least 3 times in order for it to unlock.
(Hopefully there will be a patch to make this easier to get)